CN103242860A - Liquid crystal composition and liquid crystal display device - Google Patents
Liquid crystal composition and liquid crystal display device Download PDFInfo
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- CN103242860A CN103242860A CN2013101836177A CN201310183617A CN103242860A CN 103242860 A CN103242860 A CN 103242860A CN 2013101836177 A CN2013101836177 A CN 2013101836177A CN 201310183617 A CN201310183617 A CN 201310183617A CN 103242860 A CN103242860 A CN 103242860A
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- liquid crystal
- crystal composition
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- compound
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 188
- 239000000203 mixture Substances 0.000 title claims abstract description 167
- 150000001875 compounds Chemical class 0.000 claims abstract description 158
- 239000011159 matrix material Substances 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004991 fluoroalkenyl group Chemical group 0.000 claims description 2
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 230000004044 response Effects 0.000 abstract description 7
- 238000012360 testing method Methods 0.000 description 25
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 0 CC*c1c(*)c(C*)cc(C(C)(CC)c(c(C(C)I)c2)c(C*)cc2*(OC(c(c(F)c(c(C(C)(C)c2ccc(C(C)(C)*c3ccc(*)cc3)cc2)c2)F)c2F)(F)F)=C)c1 Chemical compound CC*c1c(*)c(C*)cc(C(C)(CC)c(c(C(C)I)c2)c(C*)cc2*(OC(c(c(F)c(c(C(C)(C)c2ccc(C(C)(C)*c3ccc(*)cc3)cc2)c2)F)c2F)(F)F)=C)c1 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZRTWIJKGTUGZJY-UHFFFAOYSA-N 3,4,5-trifluorophenol Chemical compound OC1=CC(F)=C(F)C(F)=C1 ZRTWIJKGTUGZJY-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- XSMLLZPSNLQCQU-UHFFFAOYSA-N 1-bromo-2,3,5-trifluorobenzene Chemical compound FC1=CC(F)=C(F)C(Br)=C1 XSMLLZPSNLQCQU-UHFFFAOYSA-N 0.000 description 2
- ANUZKYYBDVLEEI-UHFFFAOYSA-N butane;hexane;lithium Chemical compound [Li]CCCC.CCCCCC ANUZKYYBDVLEEI-UHFFFAOYSA-N 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QOIWHSKYUNIFCV-UHFFFAOYSA-N (2-fluoro-4-propylphenyl)boronic acid Chemical compound CCCC1=CC=C(B(O)O)C(F)=C1 QOIWHSKYUNIFCV-UHFFFAOYSA-N 0.000 description 1
- WLCGYIWOKVWFLB-UHFFFAOYSA-N (4-propylphenyl)boronic acid Chemical compound CCCC1=CC=C(B(O)O)C=C1 WLCGYIWOKVWFLB-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- HWQNWWGSYSISNO-UHFFFAOYSA-N 4-bromo-2,3,5-trifluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(Br)C(F)=C1F HWQNWWGSYSISNO-UHFFFAOYSA-N 0.000 description 1
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- WQBZGMHQRORRBQ-SREVYHEPSA-N CC/C(/F)=C(\C(C)=C)/F Chemical compound CC/C(/F)=C(\C(C)=C)/F WQBZGMHQRORRBQ-SREVYHEPSA-N 0.000 description 1
- XXVTURJOQOBKEX-UHFFFAOYSA-N Cc(cc1)ccc1-c1ccc(-c(cc(c(C(Oc(cc2F)cc(F)c2F)(F)F)c2F)F)c2F)c(F)c1 Chemical compound Cc(cc1)ccc1-c1ccc(-c(cc(c(C(Oc(cc2F)cc(F)c2F)(F)F)c2F)F)c2F)c(F)c1 XXVTURJOQOBKEX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- AZSZCFSOHXEJQE-UHFFFAOYSA-N dibromodifluoromethane Chemical compound FC(F)(Br)Br AZSZCFSOHXEJQE-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- -1 hydrogen trifluoride Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- LHJSLDBKUGXPMI-UHFFFAOYSA-N tris(2-methylpropyl) borate Chemical compound CC(C)COB(OCC(C)C)OCC(C)C LHJSLDBKUGXPMI-UHFFFAOYSA-N 0.000 description 1
- IPGCWJZKTTZTSB-UHFFFAOYSA-K trisodium;trifluoride Chemical compound [F-].[F-].[F-].[Na+].[Na+].[Na+] IPGCWJZKTTZTSB-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
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- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
- C09K2019/0407—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/122—Ph-Ph
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/123—Ph-Ph-Ph
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3004—Cy-Cy
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/301—Cy-Cy-Ph
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3021—Cy-Ph-Ph-Cy
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
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- Crystallography & Structural Chemistry (AREA)
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- Liquid Crystal Substances (AREA)
Abstract
The invention provides a liquid crystal composition and application thereof. The liquid crystal composition comprises at least one compound of a general formula I and at least one compound of a general formula II. The liquid crystal composition has large dielectric anisotropy, appropriately high refractive index anisotropy, a high response speed and good low-temperature storage stability. The invention further provides an active matrix liquid crystal display device comprising the liquid crystal composition.
Description
Technical Field
The present invention relates to a liquid crystal composition, and more particularly, to a liquid crystal composition having appropriate optical anisotropy and dielectric anisotropy, a fast response speed, and good low-temperature storage stability, and an application thereof in an active matrix liquid crystal display device.
Background
The liquid crystal material is a mixture of organic rod-shaped small molecular compounds which have liquid fluidity and crystal anisotropy at a certain temperature. Liquid crystal display devices operate by utilizing optical anisotropy and dielectric anisotropy of liquid crystal materials themselves, and are now widely used. The device can be designed into various operation modes by utilizing different characteristics and operation modes of the liquid crystal material, wherein the conventional display commonly uses a TN mode (twisted nematic mode, a liquid crystal mixture has a nematic structure with a twist degree of about 90 degrees), an STN mode (super twisted nematic mode), an SBE mode (super twisted birefringence), an ECB mode (electrically controlled birefringence), a VA mode (vertical alignment), IPS (in-plane switching), and the like, and a plurality of improvement modes are made according to the above various modes.
For liquid crystal displays, liquid crystal compounds and liquid crystal media having good chemical and thermal stability, good stability to electric fields and electromagnetic radiation, suitable optical anisotropy, faster response speed, and lower threshold voltage are in line with the current demand. For active matrix addressed liquid crystal displays, the liquid crystal medium also has a high voltage holding ratio and good optical and thermal stability. In particular, for displays used in the on-board category and other outdoor uses, it is particularly desirable to have a very wide nematic temperature range.
However, the properties of liquid crystal media are contradictory, and the existing liquid crystal media cannot have the properties at the same time. Therefore, in the field of liquid crystal materials, there is a need for novel liquid crystal compositions having improved properties. In particular, for many types of applications, the liquid crystal composition must have a suitable nematic phase range, a suitable refractive index, dielectric anisotropy and low temperature storage stability.
Disclosure of Invention
The invention aims to provide a liquid crystal composition which has the characteristics of proper optical anisotropy and dielectric anisotropy, higher response speed, good low-temperature storage stability and the like. The liquid crystal composition can be applied to an AM element, and the AM element has the characteristics of short response time, high voltage holding ratio, high contrast, long service life and the like.
One aspect of the present invention provides a liquid crystal composition comprising:
at least one compound of the general formula I
at least one compound of the formula II
Wherein,
R1and R2The same or different, each independently represents an alkyl group or an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group or an alkenyloxy group having 2 to 7 carbon atoms;
R3selected from the group consisting of F, -OCF3Alkyl or alkoxy having 1 to 7 carbon atoms, and alkenyl or alkenyloxy having 2 to 7 carbon atoms, with the proviso that when p =0, R3Not being F or-OCF3；
x represents H, F, Cl, a fluoroalkyl group having 1 to 5 carbon atoms, a fluoroalkoxy group having 1 to 5 carbon atoms, a fluoroalkenyl group having 2 to 5 carbon atoms, or a fluoroalkenoxy group having 2 to 5 carbon atoms;
Z1represents a single bond, -CH = CH-, -CH2O-、-OCH2-or-CH2CH2-；
Z2Represents a single bond, -CH2O-、-CH2CH2-、-CF2O-or-COO-;
m, n and p are the same or different and each independently represents 0 or 1.
In some embodiments, the liquid crystal compositions of the present invention further comprise one or more compounds of compounds according to formula iii:
wherein,
R4and R5The same or different, each independently represent-OCF3Alkyl or alkoxy with 1-7 carbon atoms, or alkenyl or alkenyloxy with 2-7 carbon atoms;
q and r are the same or different and each independently represents 0 or 1, and q + r.gtoreq.1.
In an embodiment of the present invention, it is preferred that the compound of formula I comprises 5 to 40% by weight of the total liquid crystal composition; the compound of the general formula II accounts for 25-80% of the total weight of the liquid crystal composition; and the compound of formula III accounts for 10-40% of the total weight of the liquid crystal composition.
In some embodiments, the compound of formula I is selected from one or more of the group consisting of:
wherein,
the R is1Is selected from the group consisting of an alkyl or alkoxy group having 1 to 5 carbon atoms and an alkenyl or alkenyloxy group having 2 to 5 carbon atoms.
In some embodiments, the compound of formula II is selected from one or more compounds in the group consisting of:
wherein,
the R is2Is selected from the group consisting of an alkyl or alkoxy group having 1 to 5 carbon atoms and an alkenyl or alkenyloxy group having 2 to 5 carbon atoms.
In some embodiments, the compound of formula iii is selected from one or more compounds in the group consisting of:
wherein,
the R is4And said R5The same or different, each independently selected from the group consisting of an alkyl or alkoxy group having 1 to 5 carbon atoms and an alkenyl or alkenyloxy group having 2 to 5 carbon atoms.
Another aspect of the present invention provides a liquid crystal display device comprising the liquid crystal composition of the present invention.
A further aspect of the invention provides an active matrix liquid crystal display device comprising a liquid crystal composition of the invention.
The liquid crystal medium comprising the liquid crystal composition is determined to have the characteristics of small viscosity, good low-temperature stability, high stability to ultraviolet rays and high stability to heat by performing a combination experiment on the compounds and comparing the compound with a control.
In the present invention, unless otherwise specified, the proportions are weight ratios, all temperatures are in degrees centigrade, and the thickness of the box selected for the response time data test is 7 μm.
Drawings
FIG. 1 is a drawing of Compound A1H NMR chart;
FIG. 2 is a drawing of Compound B1H NMR chart;
FIG. 3 is a drawing of Compound C1H NMR chart;
FIG. 4 is of Compound D1H NMR chart;
FIG. 5 is of Compound E1H NMR chart;
FIG. 6 is a drawing of Compound F1H NMR chart;
FIG. 7 is a drawing of Compound G1H NMR chart;
FIG. 8 is of Compound H1H NMR chart;
FIG. 9 is of Compound I1H NMR chart;
FIG. 10 is of Compound J1H NMR chart.
Detailed Description
The invention will be illustrated below with reference to specific embodiments. It should be noted that the following examples are illustrative of the present invention, and are not intended to limit the present invention. Other combinations and various modifications within the spirit or scope of the present invention may be made without departing from the spirit or scope of the present invention.
For convenience of expression, in the following examples, the group structure of the liquid crystal composition is represented by the code listed in Table 1:
TABLE 1 radical structural code of liquid crystal compounds
Compounds of the following formula are exemplified:
the structural formula is represented by the code listed in Table 1, and can be expressed as: nCCGF, wherein n in the code represents the number of C atoms of the left alkyl group, for example, n is 3, namely, the alkyl group is-C3H7(ii) a C in the code represents cyclohexane.
The abbreviated codes of the test items in the following examples are as follows:
cp (. degree. C.): clearing points (nematic-isotropic phase transition temperature)
Δ n: optical anisotropy (589 nm, 20 ℃ C.)
Δ ε: dielectric anisotropy (1 KHz, 25 ℃ C.)
γ 1: torsional viscosity (mPas at 20 ℃ C.)
t-30℃: low temperature storage time (at-30 ℃ C.)
Wherein the refractive index anisotropy is measured by using an Abbe refractometer under a sodium lamp (589 nm) light source at 20 ℃; the dielectric test cell was of the type TN90, the cell thickness being 7 μm.
The components used in the examples below, except for the compound of formula I, can be synthesized by known methods or obtained commercially. These synthesis techniques are conventional, and the resulting liquid crystal compounds were tested to meet the standards for electronic compounds.
Preparation example 1 the synthetic route of formula a is represented as follows:
the specific process comprises the following steps:
among them, compound a1 is commercially available.
(1) Synthesis of Compound A2
21.1g of 2,3, 5-trifluorobromobenzene (A1), 16.0g of 4-n-propylphenylboronic acid, 80mL of toluene, 40mL of ethanol, 40mL of water and 22g of sodium carbonate are sequentially added into a 250mL three-necked flask, stirred for 5min, added with 0.4g of 4-triphenylphosphine palladium under the protection of nitrogen, heated and refluxed for 5 hours, subjected to aftertreatment, and purified by column chromatography to obtain a white solid A2, 22g of GC: 98.6%, yield: 88 percent.
(2) Synthesis of Compound A3
Sequentially adding 22g A2 and 120mL of anhydrous tetrahydrofuran into a 250mL three-necked bottle, cooling to-78 ℃ under the protection of nitrogen, dropwise adding 40mL of n-butyl lithium n-hexane solution (2.4 mol/L), continuously controlling the temperature to-78 ℃ after dropwise adding, stirring for 1 hour, then dropwise adding a mixture of 22g of dibromodifluoromethane and 40mL of anhydrous tetrahydrofuran into the reaction solution, continuously controlling the temperature to-78 ℃ after dropwise adding, stirring for 30 minutes, then pouring the reaction solution into an ice-water mixture, separating liquid, extracting with n-hexane, combining oil layers, washing with water to be neutral, evaporating the solvent to obtain 35g of yellow oily substance A3, directly putting into the next step for reaction without purification, and carrying out GC: 67.3%, yield: 104 percent.
(3) Synthesis of Compound A
Into a 500mL three-necked flask, 35g of oily A3 obtained in the above step, 350mL of N, N-Dimethylformamide (DMF), 10.3g of anhydrous potassium carbonate, 9.6g of 3,4, 5-trifluorophenol, were added, heated to 120 ℃, stirred for 3 hours, post-treated, and purified by column chromatography to obtain a white solid A, 11g, GC: 99.5%, yield: 26.7 percent.
In the same manner, compound C, D, E of the following formula can be prepared:
TABLE 2 liquid Crystal Properties of Compound A, C, D, E
| Compound (I) | DSC | Δε | Δn |
| A | C45.3I | 15 | 0.081 |
| C | C55.7I | 15.7 | 0.082 |
| D | C76.4N106.7I | 16.7 | 0.179 |
| E | C73.6N94.3I | 19.9 | 0.169 |
Of Compound A1FIG. 1 shows an H-NMR chart;
of compound C1FIG. 3 shows an H-NMR chart;
of Compound D1The H-NMR chart is shown in FIG. 4;
of the Compound E1The H-NMR chart is shown in FIG. 5.
Preparation example 2 the synthetic route of formula B is represented as follows:
the specific process comprises the following steps:
among them, compound B1 is commercially available.
(1) Synthesis of Compound B2
Adding 25.5g of 2,3, 5-trifluoro-4-bromobenzoic acid (B1), 100mL of toluene, 14.0g of 1, 3-propanedithiol and 19.5g of trifluoromethanesulfonic acid into a 250mL three-necked flask in sequence, heating and refluxing, dividing water for 3 hours, evaporating to remove about 50mL of toluene, cooling to room temperature under the protection of nitrogen, adding 100mL of dichloromethane into the reaction flask, cooling to-78 ℃, adding a mixture of 15g of triethylamine, 19g of 3,4, 5-trifluorophenol and 50mL of dichloromethane dropwise into the reaction flask, stirring for 1 hour under the protection of nitrogen, adding 24g of triethylamine composite hydrogen trifluoride solution dropwise into the reaction flask, adding 24g of bromine into the reaction flask after 5 minutes, continuously controlling the temperature to-78 ℃, stirring for 1 hour, naturally heating to-30 ℃, pouring the reaction solution into a mixture of 8g of sodium hydroxide and 300g of sodium trifluoride, post-treatment and purification by column chromatography gave a white solid, b216.5g, GC: 99.2, yield: 40.5 percent.
(2) Synthesis of Compound B4
14.2g of p-bromoiodobenzene (B3), 9.0g of 4-n-propyl-2-fluorobenzeneboronic acid, 60mL of toluene, 30mL of ethanol, 30mL of water and 11g of sodium carbonate are sequentially added into a 250mL three-necked flask, stirred for 5min, added with 0.2g of 4-triphenylphosphine palladium under the protection of nitrogen, heated and refluxed for 5 hours, subjected to aftertreatment, and purified by column chromatography to obtain a white-like solid B4, 13.1g of GC: 98.3%, yield: 89.4 percent.
(3) Synthesis of Compound B5
Adding 13.1g B4 and 100mL of anhydrous tetrahydrofuran into a 250mL three-neck flask, cooling to-78 ℃ under the protection of nitrogen, dropwise adding 21mL of n-butyl lithium n-hexane solution (2.4 mol/L), continuously controlling the temperature to-78 ℃, stirring for 1 hour, then dropwise adding a mixture of 12g of triisobutyl borate and 40mL of anhydrous tetrahydrofuran into the reaction flask, continuously controlling the temperature to-78 ℃, stirring for 1 hour, post-treating, and evaporating the solvent to obtain an off-white solid B59.9g, HPLC: 95%, yield: 85.8 percent.
(4) Synthesis of Compound B
5.2g B5, 8.2g B2, 50mL toluene, 25mL ethanol, 25mL water and 4.3g sodium carbonate are added into a 250mL three-necked bottle in sequence, stirred for 5min, then added with 0.1g 4-triphenylphosphine palladium under the protection of nitrogen, heated and refluxed for 6 hours, and then subjected to aftertreatment and purification by column chromatography to obtain a white solid B, 8.1g, GC: 99.8%, yield: 75 percent.
In the same manner, compound F, G, H, I, J of the following formula can be prepared:
TABLE 3 liquid Crystal Properties of Compound B, F, G, H, I, J
| Compound (I) | DSC | Δε | Δn |
| B | C111.7I | 18 | 0.181 |
| F | C148.6I | 20.2 | 0.17 |
| G | C81.8N118.1I | 19.7 | 0.126 |
| H | C81.7N87.9I | 20 | 0.127 |
| I | C99N113.4I | 22 | 0.18 |
| J | C109.3N144.1I | 17.8 | 0.225 |
Of compounds B1FIG. 2 shows an H-NMR chart;
of compound F1FIG. 6 shows an H-NMR chart;
of compound G1FIG. 7 shows an H-NMR chart;
of compound H1FIG. 8 shows an H-NMR chart;
of the Compound I1FIG. 9 shows an H-NMR chart;
of Compound J1The H-NMR chart is shown in FIG. 10.
Liquid crystal compositions were prepared according to the compounding ratios of the liquid crystal compositions specified in the following examples. The liquid crystal composition is prepared according to the conventional method in the field, such as heating, ultrasonic wave, suspension and the like, and is mixed according to the specified proportion.
Liquid crystal compositions given in the following examples were prepared and studied. The composition of each liquid crystal composition and the results of the performance parameter test thereof are shown below.
Table 4 shows the components and ratios of the liquid crystal composition of the comparative example and the results of the performance test conducted on the liquid crystal composition filled between two substrates of the liquid crystal display device, so as to compare the performance of the liquid crystal composition of the present invention.
Comparative example 1
The liquid crystal composition of comparative example 1, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared according to the compounds and weight percentages listed in table 4, and the test data are shown in the following table:
TABLE 4 liquid crystal composition formula and its test performance
Example 1
The liquid crystal composition of example 1 was prepared according to the compounds and weight percentages listed in table 5, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 5 liquid crystal composition formulations and their test properties
Example 2
The liquid crystal composition of example 2 was prepared according to the compounds and weight percentages listed in table 6, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 6 liquid crystal composition formula and its test performance
Example 3
The liquid crystal composition of example 3 was prepared according to the compounds and weight percentages listed in table 7, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 7 liquid crystal composition formulations and their test properties
Example 4
The liquid crystal composition of example 4 was prepared according to the compounds and weight percentages listed in table 8, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 8 liquid crystal composition formulations and their test properties
Example 5
The liquid crystal composition of example 5 was prepared according to the compounds and weight percentages listed in table 9, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 9 liquid crystal composition formulations and their test properties
Example 6
The liquid crystal composition of example 6 was prepared according to the compounds and weight percentages listed in table 10, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 10 liquid crystal composition formulations and their test properties
Referring to comparative example 1, as can be seen from the above test data of examples 1, 2,3, 4,5 and 6, the liquid crystal composition provided by the present invention has a small viscosity, a large dielectric anisotropy, a suitably high refractive index anisotropy, and is advantageous in response speed, good display effect and low-temperature storage stability, and suitable for use in AM display devices.
Claims (9)
1. A liquid crystal composition comprising:
at least one compound of the general formula I
at least one compound of the formula II
Wherein,
R1and R2The same or different, each independently represents an alkyl group or an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group or an alkenyloxy group having 2 to 7 carbon atoms;
R3selected from the group consisting of F, -OCF3Alkyl or alkoxy having 1 to 7 carbon atoms, and alkenyl or alkenyloxy having 2 to 7 carbon atoms, with the proviso that when p =0, R3Not being F or-OCF3；
x represents H, F, Cl, a fluoroalkyl group having 1 to 5 carbon atoms, a fluoroalkoxy group having 1 to 5 carbon atoms, a fluoroalkenyl group having 2 to 5 carbon atoms, or a fluoroalkenoxy group having 2 to 5 carbon atoms;
Z1represents a single bond, -CH = CH-, -CH2O-, -OCH2-or-CH2CH2-；
Z2Represents a single bond, -CH2O-、-CH2CH2-、-CF2O-or-COO-;
m, n and p are the same or different and each independently represents 0 or 1.
2. The liquid crystal composition of claim 1, further comprising one or more compounds from the compounds according to formula iii:
wherein,
R4and R5The same or different, each independently represent-OCF3Alkyl or alkoxy with 1-7 carbon atoms, or alkenyl or alkenyloxy with 2-7 carbon atoms;
q and r are the same or different and each independently represents 0 or 1, and q + r.gtoreq.1.
3. The liquid crystal composition of claim 2, wherein the compound of formula I comprises 5-40% of the total weight of the liquid crystal composition; the compound of the general formula II accounts for 25-80% of the total weight of the liquid crystal composition; and the compound of formula III accounts for 10-40% of the total weight of the liquid crystal composition.
4. The liquid crystal composition of claim 3, wherein the compound of formula I is selected from one or more compounds of the group consisting of:
wherein,
the R is1Is selected from the group consisting of an alkyl or alkoxy group having 1 to 5 carbon atoms and an alkenyl or alkenyloxy group having 2 to 5 carbon atoms.
5. The liquid crystal composition of claim 3, wherein the compound of formula II is selected from one or more compounds of the group consisting of:
wherein,
the R is2Is selected from the group consisting of an alkyl or alkoxy group having 1 to 5 carbon atoms and an alkenyl or alkenyloxy group having 2 to 5 carbon atoms.
6. The liquid crystal composition according to claim 3, wherein the compound of formula III is selected from one or more compounds in the group consisting of:
wherein,
the R is4And said R5The same or different, each independently selected from the group consisting of an alkyl or alkoxy group having 1 to 5 carbon atoms and an alkenyl or alkenyloxy group having 2 to 5 carbon atoms.
7. The liquid crystal composition according to any one of claims 4 to 6, wherein the liquid crystal composition comprises:
45% of compound based on the total weight of the liquid crystal composition
A compound accounting for 10 percent of the total weight of the liquid crystal composition
A compound accounting for 9 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 5 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 5 percent of the total weight of the liquid crystal composition
A compound accounting for 4 percent of the total weight of the liquid crystal composition
2% of compound based on the total weight of the liquid crystal composition
2% of compound based on the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
And
a compound accounting for 3 percent of the total weight of the liquid crystal composition
Alternatively, the liquid crystal composition comprises:
44% of compound based on the total weight of the liquid crystal composition
A compound accounting for 8 percent of the total weight of the liquid crystal composition
A compound accounting for 8 percent of the total weight of the liquid crystal composition
6 percent of compound in the total weight of the liquid crystal composition
6 percent of compound in the total weight of the liquid crystal composition
2% of compound based on the total weight of the liquid crystal composition
2% of compound based on the total weight of the liquid crystal composition
A compound accounting for 4 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 4 percent of the total weight of the liquid crystal composition
A compound accounting for 5 percent of the total weight of the liquid crystal composition
2% of compound based on the total weight of the liquid crystal composition
2% of compound based on the total weight of the liquid crystal composition
2% of compound based on the total weight of the liquid crystal composition
2% of compound based on the total weight of the liquid crystal composition
Alternatively, the liquid crystal composition comprises:
45% of compound based on the total weight of the liquid crystal composition
A compound accounting for 5 percent of the total weight of the liquid crystal composition
A compound accounting for 5 percent of the total weight of the liquid crystal composition
A compound accounting for 5 percent of the total weight of the liquid crystal composition
A compound accounting for 8 percent of the total weight of the liquid crystal composition
A compound accounting for 4 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 4 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
2% of compound based on the total weight of the liquid crystal composition
2% of compound based on the total weight of the liquid crystal composition
a compound accounting for 5 percent of the total weight of the liquid crystal composition
Alternatively, the liquid crystal composition comprises:
45% of compound based on the total weight of the liquid crystal composition
A compound accounting for 7 percent of the total weight of the liquid crystal composition
A compound accounting for 7 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 5 percent of the total weight of the liquid crystal composition
A compound accounting for 5 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 4 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
2% of compound based on the total weight of the liquid crystal composition
2% of compound based on the total weight of the liquid crystal composition
And
a compound accounting for 5 percent of the total weight of the liquid crystal composition
Alternatively, the liquid crystal composition comprises:
a compound accounting for 40 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 5 percent of the total weight of the liquid crystal composition
A compound accounting for 5 percent of the total weight of the liquid crystal composition
A compound accounting for 5 percent of the total weight of the liquid crystal composition
A compound accounting for 5 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 5 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 4 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 4 percent of the total weight of the liquid crystal composition
2% of compound based on the total weight of the liquid crystal composition
Alternatively, the liquid crystal composition comprises:
a compound accounting for 40 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 4 percent of the total weight of the liquid crystal composition
A compound accounting for 4 percent of the total weight of the liquid crystal composition
A compound accounting for 4 percent of the total weight of the liquid crystal composition
A compound accounting for 4 percent of the total weight of the liquid crystal composition
A compound accounting for 4 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 4 percent of the total weight of the liquid crystal composition
6 percent of compound in the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 4 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 3 percent of the total weight of the liquid crystal composition
A compound accounting for 4 percent of the total weight of the liquid crystal composition
a compound accounting for 4 percent of the total weight of the liquid crystal composition
8. A liquid crystal display device comprising the liquid crystal composition according to any one of claims 1 to 7.
9. An active matrix liquid crystal display device comprising the liquid crystal composition according to any one of claims 1 to 7.
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| CN108659851A (en) * | 2018-06-22 | 2018-10-16 | 烟台显华化工科技有限公司 | A kind of liquid-crystal compounds and its preparation method and application containing difluoro-methoxy bridged bond |
| CN108659853A (en) * | 2017-03-29 | 2018-10-16 | 北京八亿时空液晶科技股份有限公司 | A kind of liquid-crystal composition containing fluoroalkyl liquid-crystal compounds and its application |
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| WO2014183561A1 (en) * | 2013-05-15 | 2014-11-20 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and liquid crystal display device |
| CN104342168A (en) * | 2013-08-06 | 2015-02-11 | 江苏和成显示科技股份有限公司 | Liquid crystal composition with good low temperature storage stability and liquid crystal display device |
| CN104342168B (en) * | 2013-08-06 | 2016-08-10 | 江苏和成显示科技股份有限公司 | There is liquid-crystal composition and the liquid crystal display device of good low temperature storage stability |
| CN104371743A (en) * | 2013-08-16 | 2015-02-25 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and liquid crystal display device |
| TWI499662B (en) * | 2013-08-16 | 2015-09-11 | ||
| CN104371746B (en) * | 2013-08-16 | 2016-05-25 | 江苏和成显示科技股份有限公司 | Liquid-crystal composition and liquid crystal display device |
| CN104371746A (en) * | 2013-08-16 | 2015-02-25 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and liquid crystal display device |
| CN104629773B (en) * | 2013-11-06 | 2017-01-11 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and display device thereof |
| CN104629772B (en) * | 2013-11-06 | 2017-07-28 | 江苏和成显示科技股份有限公司 | Positive liquid crystal composition and its display device with high transmittance |
| CN108659853A (en) * | 2017-03-29 | 2018-10-16 | 北京八亿时空液晶科技股份有限公司 | A kind of liquid-crystal composition containing fluoroalkyl liquid-crystal compounds and its application |
| CN107955631A (en) * | 2017-11-22 | 2018-04-24 | 烟台显华化工科技有限公司 | A kind of liquid-crystal composition and its application |
| CN108300489A (en) * | 2018-02-09 | 2018-07-20 | 烟台显华化工科技有限公司 | A kind of liquid-crystal composition and its application |
| CN108659851A (en) * | 2018-06-22 | 2018-10-16 | 烟台显华化工科技有限公司 | A kind of liquid-crystal compounds and its preparation method and application containing difluoro-methoxy bridged bond |
| WO2019242095A1 (en) * | 2018-06-22 | 2019-12-26 | 烟台显华化工科技有限公司 | Liquid crystal compound containing a difluoromethoxy bridge bond and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103242860B (en) | 2014-11-05 |
| WO2014183561A1 (en) | 2014-11-20 |
| TW201443203A (en) | 2014-11-16 |
| TWI599639B (en) | 2017-09-21 |
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